Patent GB-901648-A (GB)
Title: A method of protecting organic materials against the action of ultraviolet light
IPC: C07D401/04
Filed: 1959-05-25
Abstract: Hydrophobic oily, fatty or waxy substances such as candles, p  floor polish, floor stains or other wood stains and coloured or uncoloured soaps, have incorporated therein an ultra-violet light proofing agent comprising an azole compound in which the two vicinal carbon atoms of the azole ring are also members of a benzene ring and the carbon atom between the two heteroatoms of the azole ring is bound to a carbon atom of a pyridine ring.  The azole compounds are benzthiazoles, benzimidazoles or benzoxazoles bound in the 2-position directly to a pyridine ring and may be unsubstituted or substituted in the benzene ring by alkyl or alkoxy groups of low molecular weight, phenyl residues or chlorine atoms and in the pyridine ring by alkyl groups of halogen atoms. Numerous examples of suitable azole compounds are given.  If the materials contain dyestuffs or pigments the azole compounds also protect the fastness to light of the dyestuffs or pigments. 0,01-10% of the azole compound calculated on the weight of the material is preferably used.  Specification 824,659 is referred to.ALSO:Compositions comprising cellulose acetate including cellulose triacetate, cellulose propionate, butyrate, acetate-propionate or acetatebutyrate, viscose solutions, nitrocellulose, synthetic resins, e.g. polyvinyl acetate, polyvinyl chloride, copolymers of vinyl chloride and vinylidene chloride, polyacrylic acid resins, polyethylene polyamides polyesters epoxy resins polystyrene resins and aldehyde resins such as phenolurea- or melamine-formaldehyde condensation products rubber balata, guttapercha and synthetic vulcanizable materials such as polychloroprene olefinic polysulphides, polybutadiene or copolymers of butadiene and styrene or of butadiene and acrylonitrile which may contain filling materials, pigments and vulcanization accelerators, are protected against ultra-violet rays by incorporating therein an azole compound in which the two vicinal carbon atoms of the azole ring are also members of a benzene ring and the carbon atom between the two hetero-atoms of the azole ring is bound to a carbon atom of a pyridine ring.  The azole compounds are benzthiazoles, benzimidazoles or benzoxazoles bound in the 2-position directly to a pyridine ring and may be unsubstituted or substituted in the benzene ring by alkyl or alkoxy groups of low molecular weight, phenyl residues or chlorine atoms and in the pyridine ring by alkyl groups or halogen atoms. Numerous examples of suitable azole compounds are given.  If the materials protected contain dyestuffs or pigments the azole compounds also protect the fastness to light of the dyestuffs or pigments. 0,01-10% of the azole compound calculated on the weight of the material to be protected is preferably used.  The azole compounds may be incorporated into the synthetic resins before or during polymerization or polycondensation.  The compositions may be used for the manufacture of fibres or films or as dressing agents for textiles or paper or as lacquers. Specification 824,659 is referred to.ALSO:Benzthiazoles, benzimidazoles and benzoxazoles which are bound in the 2-position of the azole ring directly to a carbon atom of a pyridine ring are prepared by reacting an ortho-aminothiophenol, an ortho - diaminobenzene or an ortho-aminophenol with a pyridine carboxylic acid or a functional derivative thereof, e.g. an alkyl ester, in the presence or absence of an organic solvent but preferably in the presence of an agent capable of splitting off water, e.g. boric acid, a zinc chloride melt or a polyphosphoric acid of the formula Hn + 2PnO3n + 1. in which n represents a number having a value of at least 3.  The azoles may be substituted in the benzene ring by alkyl or alkoxy groups of low molecular weight, phenyl residues or chlorine atoms and in the pyridine ring by alkyl groups or halogen atoms.  Specification 824,659 is referred to.ALSO:Textile materials, e.g. fibres, filaments, yarns, woven or knitted fabrics or felt consisting of natural or synthetic fibres such as wool, hair, silk, cotton, hemp, flax, linen, jute, ramie, cellulose acetate, including cellulose triacetate, viscose rayon, polyamides and polyesters, are protected against ultraviolet rays by treating them with an azole compound in which the two vicinal carbon atoms of the azole ring are also members of a benzene ring and the carbon atom between the two hetero-atoms of the azole ring is bound to a carbon atom of a pyridine ring.  The azole compounds are benzthiazoles, benzimidazoles or benzoxazoles bound in the 2-position directly to a pyridine ring and may be unsubstituted or substituted in the benzene ring by alkyl or alkoxy groups of low molecular weight, phenyl residues or chlorine atoms and in the pyridine ring by alkyl groups or halogen atoms. Numerous examples of suitable azole compounds are given.  If the materials protected contain dyestuffs or pigments the azole compounds also protect the fastness to light of the dyestuffs or pigments.  0.01-10% of the azole compound calculated on the weight of the material to be protected is preferably used.  The azole compounds may be applied to the textile materials in conjunction with dressing agents based on artificial resins, e.g. vinyl-acetate or derivatives of acrylic acid, starch or casein. The use of the azole compounds for optically brightening polyacrylonitrile fibres, as disclosed in Specification 824,659, is disclaimed.ALSO:Cosmetic preparations, e.g. perfumes, skin and face creams, powder, insect repellents and anti-sunburn oils and creams comprise, as ultra-violet light-proofing agents, an azole compound in which the two vicinal carbon atoms of the azole ring are also members of a benzene ring and the carbon atom between the two hetero-atoms of the azole ring is bound to a carbon atom of a pyridine ring.  The azole compounds are benzthiazoles, benzimidazoles or benzoxazoles bound in the 2-position directly to a pyridine ring and may be unsubstituted or substituted in the benzene ring by alkyl or alkoxy groups of low molecular weight, phenyl residues or chlorine atoms and in the pyridine ring by alkyl groups or halogen atoms.  Numerous examples of suitable azole compounds are given.  If the materials protected contain dyestuffs or pigments, the azole compounds also protect the fastness to light of the dyestuffs or pigments.  0.01-10% of the azole compound calculated on the weight of the material to be protected is preferably used. Examples 7-11 refer to insect repellents and sunburn oils comprising an azole compound and other compounds such as adipic acid isopropyl tetrahydrofurfuryl ester, glycol monostearate, perfumes, ethanol, benzoic acid diethylamide, phthalic acid dimethyl ester, peanut oil, paraffin oil, glycerol monostearate, cetyl alcohol, sodium cetyl sulphate, stearic acid, glycerol, toluic acid diethylamide, white beeswax and lanolin.  Specification 824,659 is referred to.